


One Night, 10 Bucks, and Food (HIGHSCHOOL AU)

by Geeks4Squeaks



Category: Supernatural
Genre: AU, Alternate Universe, Cousin, Cute, Dean - Freeform, Dean Winchester - Freeform, Double Date, Drama, F/M, Fluff, Happy Ending, Highschool AU, Highschool AU Date, Lisa - Freeform, Pool, Protective Dean Winchester, Sam Winchester - Freeform, Supernatural - Freeform, Surprise Date, Third Wheel, WIN, date, highschool, kiss, prank, shy character, slight angst, trick - Freeform
Language: English
Status: Completed
Published: 2019-07-26
Updated: 2019-07-26
Packaged: 2020-07-20 02:15:51
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 3,764
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19984393
Author URL: https://archiveofourown.org/users/Geeks4Squeaks/pseuds/Geeks4Squeaks
Summary: REQUEST___________Highschool AU (No hunting) where Dean Winchester makes a deal with Lisa. For only one night, ten dollars, and food, Dean goes on a date with Lisa's best friend (you) to prove a point to her relatives. Not all goes as planned.





	One Night, 10 Bucks, and Food (HIGHSCHOOL AU)

**Author's Note:**

> FANDOM REQUESTS ARE ALWAYS OPEN! Just give me the fandom, prompt, some details, etc. and I will whip something up. It has to be a fandom I know well/am comfortable with. I have the right to refuse any request.

Deans POV

~*~*~*~*~*~

I lean on my shoulder on the side of my locker, twirling a pencil in my hand as I eyed down a pretty girl in red. She glances at me, giggles, and looks away. I wink at her and she repeats the flirty process once more. This is a regular game to play, wink, flirt, whatever. Kennedy was her name, wasn't it? She wasn't half bad looking I suppose. I sigh, the brief thought of actually taking her out on a date quickly crossing my mind. The pleasant thought is quickly shattered with a rather desperate call of my name.

"Dean!" Lisa calls from the end of the hall. I roll my eyes and turn my shoulder to meet her, folding my arms in front of myself. 

"That's my name, don't wear it out," I reply with a coy smile. Lisa clutches her books against her chest, her dark hair neatly curled and her eyes rolling carelessly. 

"Are you free tonight?" She asks, raising her eyebrow. I pause for a second, Dad would be at work still which would just leave Sammy and me at home. Alone. Technically, Sammy and I were always free, as much as we hated it.

"Depends on the reason," I reply cheekily. Lisa rolls her eyes once more and looks away slightly as if contemplating her next words.

"I need someone to come with me on a date." She says boldly, pleading me with her pretty eyes.

"You're asking me out?" I smirk- a newfound interest in Lisa burning in my head. I raise my arms up and prop my elbow up. 

"Ew never. No, what I am asking is to come along as a double date with me and my boyfriend Devin. I have a good friend, Y/N, that I invited as well. Her last boyfriend dumped her about a week ago and she just needs to have a bit of fun. Plus it's her family's bar so her cousins and stuff are going to be there and wondering who the hell she is dating." Lisa explains. She licks her lips quickly, waiting for my answer. 

"And she couldn't just I don't know... Tell her family she broke up like a normal family." I ask, Lisa. Half of me was bummed she wasn't asking me out- she wasn't bad looking either. Lisa did have a boyfriend, however. Bummer indeed.

"Well, its more of a pride kinda thing. They give her a hard time and all and tonight is kinda like a 'haha in your face' sort of thing. Trust me it's going to be fun. There will be food, music, and if you still refuse to go I'll pay you ten bucks for just one night." Lisa sighs, checking the clock for the end of lunch period. "And I kind of sorta already booked four people.." She admits.

"One night, food, and ten bucks." I agreed she let out a sigh of relief and smiles. The bell rings and students began milling around in the halls, lockers slam shut, and chatter crowd the halls.

"Who even is this girl. I mean have I met her? Don't recognize the name," I ask Lisa. We walk together, occasionally grunting as we made our way through the tightly packed hallway. My mind kept drifting to the newly discovered name; Y/N. Still not familiar. As if on cue, Lisa quickly speaks.

"It's Y/N, remember that, and she's the cute H/C one that hangs around us all the time. I am surprised you haven't noticed her." Lisa responds. "You notice everything else that has boobs."

"There are a lot of cute H/C girls that hang around you," I say not recalling any specific cute H/C girls around Lisa. I didn't even bother to snap at her last remark either, it's not like she was entirely wrong.

"Jeez, well she sure notices you," Lisa says smirking. 

"Wait, what?" I ask but Lisa had already turned on her heel and skipped through to her classroom, disappearing into the mess of high school kids. A certain spark of interest causes me to pause. She is interested in me, but hasn't come up to talk to me yet? Odd...

I'm interested.

So... What was her name again?

*~*~*~*~*

YOUR POV  
\---–----––--––—

"Black or Blue?" I ask Lisa who was sitting on my bed, her hair swept to one side and a nice off the shoulder blouse and tight jeans on. She always knew how to rock any outfit.

"Black. Looks sexy," she responds wriggling her eyebrows. I roll my eyes and slip on the sleek black halter top.

"And who am I trying to look sexy for anyway? " I scoff and sigh.

"Uh hello, Dean," Lisa says, nibbling on some crackers left on my bed. Lisa gives me a friendly wink.

"It's literally one night and you paid him to do it. He probably doesn't even know my name. Every time I try to flirt with him or talk to him another girl zips to his side. He doesn't even know I exist," I mumble doubtfully.

"Okay, maybe your form of 'flirting' isn't as-"

"That was a rhetorical statement," I remark. "But my point still stands." Dean always seemed to be interested in the cheerleaders, the top of class girls, the bold girls. I was none of those. I was so... ordinary. 

"Oh he knows your name-" Lisa blurts out but I interrupt her.

"How many times have you told him?" I tease.

"That's not the point. The point is yea he might be getting food and all but it's all about you tonight! Your cousins are jerks and we're going to show them up," Lisa smiles coyly, crossing her legs in front of her. Lisa had been my best friend since middle school, always starting and ending mischief and trouble, especially with my family. 

"I don't feel like that's the only reason. I know you dislike my cousins and all but there is something else to this, isn't there?" I ask, leaning forward to face her and she smiles and shrugs innocently. Before I can interrogate her any more, the doorbell rings once, then three more times rapidly. Devin- Lisa's slightly annoying but friendly boyfriend.

"That will be the boys." She smiles and we quickly make our way down the stairs.

\----

Lisa and I were seated next to each other in the back, Devin is driving and Dean is in the passenger seat, currently picking at his fingers. Every once in a while he takes a quick glance at the mirror at us and every time I would catch him he would quickly look away.

"Soo, Dean, what did you do with Sam?" Lisa asks, attempting to break the silence.

"At friends studying or playing or something," he responds gently.

"You have a younger brother?" I ask. Dean nods and smiles, this time looking back at me with curiosity and interest. Even in the dark, I can make out his vibrant green eyes, flashing with each street light we pass. 

"Twelve years old. He is a smart kid, floppy brown hair. You might have seen him around the school." He explains as moves his hands up around his head as if floppy brown hair was going to appear. I chuckle softly.

"No, I haven't," I say, taking a long glance out of the window. Silence greets us once more before familiar bright bar lights fill begin casting odd shadows and lights in the car. 

"Gordon's Gourmet," Devin says as he swings the car around, parking crookedly. A true Gourmet around here- bar food and cold drinks. 

Lisa climbs out quickly, practically attaching herself to Devin's side. A creak draws my attention back to the door which I was supposed to be getting out of. Instead, Dean was holding the door open, his hand stretching outwardly, letting me take hold of his hand and climb out of the car.

"Thank you," I mumble. Dean nods before letting go and tucking his hands into the front pockets of his leather jacket. Still, I can't help but smile softly. 

We walk in as a group, Devin slings his arm loosely Lisa's waist we make our way out of the parking lot and into the bar. She giggles and nuzzles his neck. I look away quickly, side glancing Dean who is looking at the plastic menus taped to the wall. He seems awfully hungry judging by the way his mouth was twitching as he read half the menu, licking his lips slightly each time. 

"Y/N! How've you been?" Uncle Gordon bellows from behind the bar counter. I glance at Lisa who gave me a thumbs up and she picks a booth for four. My uncle is a loud, obnoxious sort of man, which is perfect for a job as rowdy as he runs. 

"Pretty good, how about you, old-timer?" I ask him, wit and sarcasm lacing my words. He smiles, his plump cheeks shining in the bar light.

"Real good, girly! What do-" he was interrupted by the sound of breaking glass from the back room. "One moment," he says as he wobbles back to the kitchen and begins shouting incoherent things. I would be concerned had it been any other bar, but this was normal as the family was quite clumsy. 

Ted, my youngest cousin, slides in across from me, wiping his hands on his apron before resting his forearms against the bar top. Ted was a difficult boy to deal with. He was always nitpicking on others or stirring up trouble, it was as if he lived for drama. To put it bluntly, Ted was definitely not my favorite cousin. 

"Hey Y/N, here with Lisa and them I suppose?" Ted asks. I nod to him wearily and he smirks, a devilish flame to his eyes. A jolt of anxiety runs through me, anticipating his next move or harsh words. I was used to this kind of treatment, but the anger and anxiety he gave me were always like the first time. It always stung. 

"So which one is yours?" He asks, a smirk playing at his lips.

"What?" I ask, tilting my head to the side. Which what? I glance back at Lisa and Devin before quickly looking back at Ted. 

"You said you had a boyfriend. That thin little sissy with dark hair or the girl? Didn't know you swung that way." He snorts, gesturing to Lisa and Devin who were giggling as Devin made a small tower out of crayons. He kept chortling at his own 'joke' and quite frankly I hope he chokes on his tongue.

His 'jokes' and teases were childish, and I knew that I shouldn't give in to the naive anger, but it was hard. It was a stressful week and Ted was being a dick. I sigh angrily, ready to give Ted an earful before someone's arm slips around my lower belly. His hand is warm as it rests on my hip firmly. The whole gesture takes me by surprise. Even the musky scent mixed with... was that watermelon soap? Oh yes, definitely watermelon soap. 

"Neither." A familiar, low grumble responds. I did all I could to not burst out in laughing in both relief and sheer disbelief. First of all, Dean Winchester's hands are on me, the heat from his body rippling across my back already. Second, it's the first time in a long time I have been able to see utter defeat and fear written upon my cousin's face. I look up at Dean whose eyes are narrowed in a challenging way. I quickly look back to Ted who had dropped his gaze and turned on his heel to the kitchens, shaking his head slightly.

"Gotta' wash dishes..." Ted mumbles, disappearing around the corner and into the kitchens.

"Come on, the waitress is already there," Dean says, walking away, a hint of anger in his voice. The warmth on my lower back was still there, however. The waitress had already taken Lisa and Devon's order, she was now eying down the two of us. 

His arm was still slung gently across as he led me to the seats. I scoot in closest to the window and Dean took his place beside me, resting the arm that was once warm against my side above me on the wooden top of the short booth. I miss it already.

"Alright, what can I get you all to drink tonight?" the waitress asks, tapping her pen on her little notebook happily. Lisa quickly glances at Dean as if pleading him to behave. Dean gives her a little smirk before placing his order. 

"Coke, please," Dean says. Lisa sighs gently and resumes her sweet smile. The waitresses eyes meet mine.

"Just lemonade, thanks," I say. She nods and walks away, her hips swaying as she disappears into the kitchens too. 

"You know your family is kind of jerks," Dean says, toying with the napkin lying out in front of him. I shrug, he wasn't entirely wrong. 

"They mean well, most of the time," I reply. "Thank you, by the way, for putting a little scare into my cousin." He hums in response, a gentle smile playing on his pink lips. 

A few minutes pass by as the duo across Dean and me coo and tease each other. It's a slightly disturbing scene as they're either giggling and poking at each other's faces or devouring each other faces. It's awkward alright. Dean and I make small talk every now and then, awaiting our food. Every now and then Dean makes quick glances over to me, sometimes longer and paired with a coy smirk. The process continues before I work up enough nerve to ask.

"Why do you keep doing that?" I ask, my eyes meeting his playfully.

"What?" Dean asks innocently though his face said otherwise. 

"You keep looking at me," I reply. "Do I have something on my face, or what?" I lightly tease - though, in all honesty, I was slightly anxious that I did have something on my face.

"You could say that," He nods his head, winking as he turns to meet the waitress sauntering back over to the table with our drinks. The waitress took out orders and was back in less than five minutes. It took nearly ten minutes to gobble down our food before we left the seats. Devin and Dean wander off to the jukebox where they struck up a conversation about cars and other 'manly-macho' stuff. I hung close to Lisa, fearfully of awkwardness set in, but she solved it quickly. 

"Alright, couple verses couple?" Lisa asks, gesturing to the empty pool table in front of us. 

"Haha, 'couple-'" I begin to mock Lisa before a pool stick is shoved into my hands. Dean and I weren't even a couple, yet. Leave it up to Lisa to do this sort of thing. Dean, however, didn't skip a beat as he grabs the pool stick from my hands.

"Yeah, and you two are going down," Dean snaps, scowling playfully and Devin and Lisa. Lisa only rolls her eyes as she sets the table up. A gentle blush began to creep up my cheeks, but I didn't bother to hide it.

Lisa and Devin powder their sticks, talking quietly to each other. Dean leans into my side, his lips almost brushing my ear. Tingles run down my spine as he whispers uncertainly.

"You do know how to play, right?" He asks, a gentle concern. I scoff, giving him a playful elbow to the ribs.

"Yeah, it's the only thing I am half decent at," I reply, snatching the pool stick back from him. Confidence grew in my chest. I want to do well, for Dean.

-

"And the eight-ball is in," Dean says slowly, his voice low and smooth as he bumps the black eight-ball into a corner pocket. We turn and high five each other - victorious! His hand doesn't slip away from mine, though. His hand stays put in a gentle clasp, intertwined in mine. I don't try to pull away, only letting my eyes drop to the floor. 

Lisa and Devin pout, mumbling amongst themselves as they return the pool sticks to the rack.

"You're not so bad at this," Dean teases, his teasing smile returning. God. I really liked his smile.

"Hey, I told you so," I chuckle, swinging my arm softly as I meet his apple-green eyes. His mouth hangs open for a moment, caught in silent awe.

"Are we ready to head out?" Devin asks, spinning the keychain in his hand absently. Dean gives my hand a gentle squeeze and he lets go. I wipe my clammy hands on my pants, hoping he doesn't mind. I nod and we head for the door. 

We all wave Gordon and Ted goodbye, well, except for Dean. Dean gives Ted a dark glare before suddenly giving him a smirk and winking. Ted shifts uncomfortably, his smile fading and turns into the kitchen. I can only laugh. 

"Geez, what was that for?" I ask, giggling as we climb into the car. Lisa took shotgun this time, already hand and hand with Devin. Dean takes the other side, sliding in close to me.

"What do you mean?" Dean scoffs, a smirk growing on his face. He knows exactly what I mean. He always seems to. I shake my head, a smile growing on my face.

"Making Ted squirm, I mean it was funny, don't get me wrong," I say. "Did you only do it because you aren't going to see him again? Like giving him a visual souvenir to cower at for the rest of his life, or..." I let my words trail off, simply imagining Ted replaying the scene of Dean glaring at him. I hope Ted cowers forever at the thought. 

Dean's smirk falters and his brows furrow.

"I won't see him again? What is that supposed to mean?" Dean asks softly. I then realize he isn't completely joking and my heart flutters. I feel bad, guilty, for hurting him. 

"Well I just- I just thought that you wouldn't come back, or maybe you would to eat sometime maybe but-" I stammer, nerves and anxiety fueling my words. Dean cuts me off.

"I was planning to go again. With you." Dean states bluntly. I was thankful for the dark night, for it hid my tomato-red face. My heart seems to skip a beat and I fall silent. "This was a date, right?"

"O-Oh, uh, yes... Yeah, it was." I reply, my mouth drying. "I just thought you came with because Lisa talked you into it. I just thought you- I don't know... didn't want me?" my words seem to die in my mouth, withering away to silence. The only sounds are the soft chatter of Lisa and Devin upfront and the familiar hum of the car. 

"Why would you think that?" Dean asks in a hushed tone. "Okay, Lisa did talk me into that but I really enjoyed it. I really like ya'." Dean corrects himself and we both break out into a quiet, relieved laugh. 

"Okay... then it was a date," I confirm quietly. Dean's familiar smirk returns and he nudges my arm.

"Atta' girl," he replies quietly before turning away, watching the moonlit landscape blur by. The rest of the car ride home was fairly quiet. Devin pulls into my driveway nearly ten minutes later and Dean hurries out his door to open mine. I laugh, giving him a teasing curtsy and in return, Dean gives me a playfull low bow as if he was a butler. I wait away from the car slightly as Lisa and Devin said their goodbyes. Goodbye meaning half a makeout session and sweet nothings for five minutes. Lisa was staying overnight, and I felt rude to just leave her outside, but it was getting awkward. 

Dean rubs the back of his neck, glancing to the two lovebirds before shaking his head.

"Well, they're busy at the moment. Mind if I walk you to the door?" he asks, offering his hand. 

"What a gentleman, of course," I say, taking his hand. Dean smiles, blush spreading across his face like a wildfire, which surprises me. We reach my doorstep in no time, standing under the soft glow of the porch light. Dean takes both of my hands in his, biting his lip slightly. 

"So, Monday at seven, sound good?" Dean asks, his green eyes flickering joyfully to mine. I smile, excitement rushing through me. 

"Sounds great," I reply. Another wave of silence greets us, and Dean traces small circles into my hands with his thumb absently. He decides to break the silence, one of his hands snaking lazily around my waist, the other nearly touching my jaw. 

"Y/N, can I kiss you?" Dean whispers, his eyes flicking to my lips. 

For the love of God, yes. Please.

"Yes," I reply breathy. The smile on my lips land on his as his hand gentle cups my jaw and cheek. His lips are incredibly soft, warm, and tasted faintly of mint gum. I like it. The moment ends far too quickly as the clicking of Lisa's heels draws near. Dean pulls away, studying my face for a second before backing away from me. He gives me a genuine, soft smile before winking. 

"Monday at seven, okay?" Dean asks as he walks slowly backward off my porch. I can only nod as I turn away, walking into the warmth of my house and shutting my door. I lightly trace my lips, already wanting the feel Dean's lips against mine again. I could barely contain my excitement as I ran upstairs to my bedroom, awaiting Lisa.

\---

3rd POV

"Obviously you like her, which is good. Very good," Lisa says happily. Dean shrugs and nods his head, his eyes dropping to the ground.

"She's different. Not stuck up and fake. Quiet. Smart. I needed a change..." Deans trails off, brushing his thumb over his lips absently.

"Well, good. She's a good girl," Lisa sighs before handing a ten-dollar bill to Dean. "Here's your ten bucks." Dean shakes his hand, pushing the money away from him gently. 

"Don't need it." He says. Lisa scoffs, folding her arms in front of her. 

"Dean Winchester, turning down ten dollars," Lisa states, baffled. 

"Money isn't really 'happiness," Dean says quietly, sticking his hands in his pockets before quickly taking them out and pointing at her bedroom window. He stares up content with a small smile on his lips. "Girls like her are."

**Author's Note:**

> FANDOM REQUESTS ARE ALWAYS OPEN! Just give me the fandom, prompt, some details, etc. and I will whip something up. It has to be a fandom I know well/am comfortable with. I have the right to refuse any request.


End file.
